1-(2-Hydroxyethyl)-2-pyrrolidinone → 3-Fluoro-5-piperidin-1-yl-N-[4-(pyridin-4-ylmethoxy)-1-naphthyl]benzamide

HRID 1171361

Reaction equation

HRID 1171361 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([NH:12][C:13](=[O:19])OC(C)(C)C)=[CH:4][CH:3]=1.[F:20][C:21]1[CH:22]=[C:23]([CH:27]=[C:28]([N:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)[CH:29]=1)C(O)=O.O[CH2:37][CH2:38][N:39]1[CH2:43][CH2:42][CH2:41][C:40]1=O>>[F:20][C:21]1[CH:22]=[C:23]([CH:27]=[C:28]([N:30]2[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]2)[CH:29]=1)[C:13]([NH:12][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([O:1][CH2:43][C:42]2[CH:37]=[CH:38][N:39]=[CH:40][CH:41]=2)=[CH:3][CH:4]=1)=[O:19]

Participants

4

Reactant 3

HCID 769801-(2-Hydroxyethyl)-2-pyrrolidinoneHCID 10923237tert-Butyl (4-hydroxynaphthalen-1-yl)carbamateHCID 595531803-Fluoro-5-piperidinylbenzoic acid

Product 1

HCID 595532863-Fluoro-5-piperidin-1-yl-N-[4-(pyridin-4-ylmethoxy)-1-naphthyl]benzamide

Procedure

Compound is prepared from tert-butyl (4-hydroxy-1-naphthyl)carbamate, 3-fluoro-5-piperidin-1-yl-benzoic acid and 1-(2-hydroxy-ethyl)-pyrrolidin-2-one according to conditions described in general procedure D. A pink solid is produced (38 mg). Mp: 69-71° C.; 1H NMR (300 MHz, DMSO-d6) δ 1.58 (s, 6H), 3.28 (s, 4H), 5.42 (s, 2H), 6.95 (d, J=8.4 Hz, 1H), 7.06 (d, J=8.1Hz, 1H), 7.15 (d, J=6.9 Hz, 1H), 7.44 (s, 1H), 7.55-7.60 (m, 4H), 7.85-7.92 (m, 1H), 8.30-8.38 (m, 1H), 8.60-8.63 (m, 1H), 10.26 (s, 1H); MS 456 (M+1).

Workup

  1. customA pink solid is produced (38 mg)

Sources & evidence

ORD record
ord-aa75914666b045e7a55a3bf6d4e827eb
Source dataset
uspto-grants-2010_11
Patent number
US07829560B2

Linked notes

Loading…